Methane → HCID 86651680, compound

HRID 337640Notes

Reaction equation

HRID 337640 reaction equation
[CH3:1][O:2][C:3]1[C:10](/[CH:11]=[CH:12]/[CH2:13][O:14][CH3:15])=[CH:9][C:8](/[CH:16]=[CH:17]/[CH2:18][O:19][CH3:20])=[CH:7][C:4]=1[CH:5]=[O:6].C>CCOC(C)=O.[Pd]>[CH3:1][O:2][C:3]1[C:10]([CH2:11][CH2:12][CH2:13][O:14][CH3:15])=[CH:9][C:8]([CH2:16][CH2:17][CH2:18][O:19][CH3:20])=[CH:7][C:4]=1[CH:5]=[O:6]

Participants

5

Reactant 2

HCID 297MethaneHCID 86651681HCID 86651681, compound

Product 1

HCID 86651680HCID 86651680, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-Methoxy-3,5-bis[(1E)-3-methoxyprop-1-en-1-yl]benzaldehyde (1 eq.) from the previous step and 10% w/w palladium over charcoal (0.1 eq.) were suspended in EtOAc (0.1 M). The vessel was then evacuated and purged with H2. Under a balloon-filled H2 atmosphere, the reaction suspension was stirred at RT for 4 h. The reaction suspension was then quenched with dichloromethane and filtered through a bed of celite. Concentration of the filtrate in vacuo to afford the crude product as a yellow oil. Further purification by way of flash chromatography (SiO2, Hex→EtOAc) afforded the title compound as a colorless oil.

Workup

  1. customThe vessel was then evacuated
  2. custompurged with H2
  3. customThe reaction suspension was then quenched with dichloromethane
  4. filtrationfiltered through a bed of celite
  5. customConcentration of the filtrate in vacuo to afford the crude product as a yellow oil
  6. customFurther purification by way of flash chromatography (SiO2, Hex→EtOAc)

Sources & evidence

ORD record
ord-7f3807ce626843efb974aabb1acac498
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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